Aliphatic primary amines are important compounds in domestic and industrial application fields and have been used as raw materials for production of surfactants, fiber-treating agents, etc.
The aliphatic primary amines have been produced by various processes. As one of the production processes, there is known the method of contacting an aliphatic alcohol with ammonia and hydrogen in the presence of a catalyst. In the catalytic reaction, there has been used a nickel/copper-based catalyst or a noble metal-based catalyst.
As the process for producing amines from aliphatic alcohols using the nickel/copper-based catalyst, there is disclosed, for example, the process for producing amines from a primary or secondary alcohol and ammonia or a primary or secondary amine using hydrogen in the presence of a zirconium/copper/nickel catalyst in which a composition containing an oxygen-containing zirconium compound in an amount of 20 to 85% by weight in terms of ZrO2, an oxygen-containing copper compound in an amount of 1 to 30% by weight in terms of CuO, an oxygen-containing nickel compound in an amount of 30 to 70% by weight in terms of NiO, an oxygen-containing molybdenum compound in an amount of 0.1 to 5% by weight in terms of MoO3, and an oxygen-containing aluminum and/or manganese compound in an amount of 0 to 10% by weight in terms of Al2O3 or MnO2 is used as a catalytically active material (refer to JP 8-176074A). Also, there is disclosed the process for producing amines from a primary or secondary alcohol and a nitrogen compound selected from the group consisting of ammonia and a primary or secondary amine at a temperature of 80 to 250° C. under a pressure of 0.1 to 40 MPa using hydrogen in the presence of a catalyst containing zirconium, copper and nickel but no oxygen-containing cobalt or molybdenum compound (refer to JP 11-180967A).
However, in these conventional techniques, the reactivity tends to be insufficient and the selectivity tends to be low.